scholarly journals A Continuous-Flow, Two-Step, Metal-Free Process for the Synthesis of Differently Substituted Chiral 1,2-Diamino Derivatives

Synthesis ◽  
2018 ◽  
Vol 50 (07) ◽  
pp. 1430-1438
Author(s):  
Maurizio Benaglia ◽  
Margherita Pirola ◽  
Maria Compostella ◽  
Laura Raimondi ◽  
Alessandra Puglisi
Keyword(s):  
Continuous Flow ◽  
Catalytic Synthesis ◽  
Flow Conditions ◽  
Reaction Conditions ◽  
Flow Process ◽  
Preliminary Screening ◽  
Metal Free ◽  
Free Process ◽  
Continuous Flow Process ◽  
Nitro Reduction

The enantioselective organocatalytic reduction of aryl-substituted nitroenamines was successfully performed under continuous-flow conditions. After a preliminary screening with a 10-μL microreactor, to establish the best reaction conditions, the reduction was scaled up in a 0.5-mL mesoreactor, without appreciable loss of enantioselectivity, that remained constantly higher than 90%. The in-flow nitro reduction was also accomplished, either by Raney nickel catalyzed hydrogenation or by a metal-free methodology based on the use of the very inexpensive and readily available reducing agent trichlorosilane. The final aim is to develop a two-step, continuous-flow process for the stereo­selective, metal-free, catalytic synthesis of differently functionalized chiral 1,2-diamines.

scholarly journals Development of an efficient and sustainable synthesis of 2-(3-methyl-1H-1,2,4-triazol-1-yl) acetic acid under continuous-flow conditions

2020 ◽  
Vol 22 (12) ◽  
pp. 3748-3758 ◽  
Author(s):  
Simone Tortoioli ◽  
Astrid Friedli ◽  
Alice Prud'homme ◽  
Sylvia Richard-Bildstein ◽  
Philipp Kohler ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Continuous Flow ◽  
Triazole Ring ◽  
Flow Conditions ◽  
Metal Free ◽  
Free Process ◽  
Efficient Construction

A novel, metal-free process for the challenging synthesis of 1,2,4-triazoles is reported, which features an efficient construction of the triazole ring under flow conditions.

A Multi-Step Continuous Flow Process for the N-Demethylation of Alkaloids

2013 ◽  
Vol 66 (2) ◽  
pp. 178 ◽  
Author(s):  
Yuji Nakano ◽  
G. Paul Savage ◽  
Simon Saubern ◽  
Peter J. Scammells ◽  
Anastasios Polyzos
Keyword(s):  
Continuous Flow ◽  
Flow Conditions ◽  
Flow Process ◽  
Continuous Flow Process

Dextromethorphan was N-demethylated using the non-classical Polonovski reaction under continuous flow conditions, in two steps: initial N-oxidation with m-chloroperbenzoic acid followed by iron-catalysed N-demethylation of the resulting N-oxide.

scholarly journals Development of an Efficient and Sustainable Synthesis of 2-(3-Methyl-1H-1,2,4-Triazol-1-Yl) Acetic Acid Under Continuous-Flow Conditions

2020 ◽  
Author(s):  
Simone Tortoioli ◽  
Astrid Friedli ◽  
Alice Prud’homme ◽  
Sylvia Richard-Bildstein ◽  
Philipp Kohler ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Continuous Flow ◽  
Flow Reactor ◽  
Environmentally Benign ◽  
Sustainable Construction ◽  
Flow Conditions ◽  
Step Method ◽  
Metal Free ◽  
Free Process ◽  
Synthetic Routes

A novel, metal-free process for the challenging synthesis of 2-(3-methyl-1<i>H</i>-1,2,4-triazol-1-yl) acetic acid (<b>1</b>) is reported, which features an efficient condensation for the triazole build-up under flow conditions. This continuous, two-step method is atom economical, highly selective and environmentally benign, due to the avoidance of chromatography and isolation steps. Compared to the earlier batch synthetic routes, higher yields were achieved in a flow reactor. In addition, a highly energetic intermediate could be controlled and handled in a safe manner. To generalize the established route, several triazoles were finally prepared under the described conditions, confirming that the methodology could find useful applications for the rapid and sustainable construction of differentially functionalized 1,2,4-triazoles.

scholarly journals Development of an Efficient and Sustainable Synthesis of 2-(3-Methyl-1H-1,2,4-Triazol-1-Yl) Acetic Acid Under Continuous-Flow Conditions

2020 ◽  
Author(s):  
Simone Tortoioli ◽  
Astrid Friedli ◽  
Alice Prud’homme ◽  
Sylvia Richard-Bildstein ◽  
Philipp Kohler ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Continuous Flow ◽  
Flow Reactor ◽  
Environmentally Benign ◽  
Sustainable Construction ◽  
Flow Conditions ◽  
Step Method ◽  
Metal Free ◽  
Free Process ◽  
Synthetic Routes

A novel, metal-free process for the challenging synthesis of 2-(3-methyl-1<i>H</i>-1,2,4-triazol-1-yl) acetic acid (<b>1</b>) is reported, which features an efficient condensation for the triazole build-up under flow conditions. This continuous, two-step method is atom economical, highly selective and environmentally benign, due to the avoidance of chromatography and isolation steps. Compared to the earlier batch synthetic routes, higher yields were achieved in a flow reactor. In addition, a highly energetic intermediate could be controlled and handled in a safe manner. To generalize the established route, several triazoles were finally prepared under the described conditions, confirming that the methodology could find useful applications for the rapid and sustainable construction of differentially functionalized 1,2,4-triazoles.

A Continuous Flow Process for LSN647712 via Double Organometallic Additions to Dimethylcarbamyl Chloride

2021 ◽  
Author(s):  
Hui Li ◽  
Jillian W. Sheeran ◽  
David Kouvchinov ◽  
Andrew M. Clausen ◽  
Ian T. Crouch ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Flow Process ◽  
Continuous Flow Process

Assessing inter- and intramolecular continuous-flow strategies towards methylphenidate (Ritalin) hydrochloride

2017 ◽  
Vol 2 (2) ◽  
pp. 149-158 ◽  
Author(s):  
Romaric Gérardy ◽  
Marc Winter ◽  
Alessandra Vizza ◽  
Jean-Christophe M. Monbaliu
Keyword(s):  
Continuous Flow ◽  
Flow Process ◽  
Continuous Flow Process

Development of a scalable continuous-flow process towards enriched threo-methylphenidate (Ritalin) hydrochloride.

Continuous-Flow Process for Selective Mononitration of 1-Methyl-4-(methylsulfonyl)benzene

2016 ◽  
Vol 20 (2) ◽  
pp. 199-203 ◽  
Author(s):  
Zhiqun Yu ◽  
Pengcheng Zhou ◽  
Jiming Liu ◽  
Wenzuo Wang ◽  
Chuanming Yu ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Flow Process ◽  
Continuous Flow Process

scholarly journals The Eschenmoser coupling reaction under continuous-flow conditions

2011 ◽  
Vol 7 ◽  
pp. 1164-1172 ◽  
Author(s):  
Sukhdeep Singh ◽  
J Michael Köhler ◽  
Andreas Schober ◽  
G Alexander Groß
Keyword(s):  
Continuous Flow ◽  
Elevated Temperatures ◽  
Reaction Times ◽  
Coupling Reaction ◽  
Flow Chemistry ◽  
Flow Conditions ◽  
Reaction Conditions ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Reaction Proceeds

The Eschenmoser coupling is a useful carbon–carbon bond forming reaction which has been used in various different synthesis strategies. The reaction proceeds smoothly if S-alkylated ternary thioamides or thiolactames are used. In the case of S-alkylated secondary thioamides or thiolactames, the Eschenmoser coupling needs prolonged reaction times and elevated temperatures to deliver valuable yields. We have used a flow chemistry system to promote the Eschenmoser coupling under enhanced reaction conditions in order to convert the demanding precursors such as S-alkylated secondary thioamides and thiolactames in an efficient way. Under pressurized reaction conditions at about 220 °C, the desired Eschenmoser coupling products were obtained within 70 s residence time. The reaction kinetics was investigated and 15 examples of different building block combinations are given.

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